The present invention relates to a class of sulfonylurea compounds, agriculturally suitable compositions containing them and their method-of-use as pre-emergent and/or post-emergent herbicides or plant growth regulants.
Sulfonylurea compounds exhibiting herbicidal activity are disclosed in U.S. Pat. Nos. 4,127,405 and 4,169,719. Herbicidal benzenesulfonylurea compounds containing an ortho-carboxy ester group are disclosed in U.S. Pat. No. 4,383,113.
European Application No. 84,224, published July 27, 1983 discloses herbicidal sulfonylureas such as ##STR1##
European Application No. 9419 published Apr. 2, 1980 discloses herbicidal sulfonylureas such as ##STR2## where ##STR3## R.sub.4 is Cl, Br, F, NO.sub.2, CH.sub.3, OCH.sub.3, CF.sub.3 or S(O).sub.n R.sub.3 ;
X is CH.sub.3 or OCH.sub.3 ; and PA1 Y is CH.sub.2 F, CH.sub.2 Cl, CH.sub.2 Br, C.sub.2 -C.sub.4 alkenyl, etc. PA1 R.sub.4 is CH.sub.3, CH.sub.2 CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, F, Cl, Br, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.19 ; PA1 R.sub.5 is C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, CO.sub.2 R.sub.15, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.19 ; PA1 R.sub.6 is Cl, NO.sub.2, CO.sub.2 CH.sub.3, CO.sub.2 CH.sub.2 CH.sub.3, SO.sub.2 N(CH.sub.3).sub.2, OSO.sub.2 CH.sub.3, SO.sub.2 CH.sub.3, SO.sub.2 CH.sub.2 CH.sub.3, OCH.sub.3 or OCH.sub.2 CH.sub.3 ; PA1 R.sub.7 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.8 is H, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 R.sub.9 is H or CH.sub.3 ; PA1 R.sub.10 is H or CH.sub.3 ; PA1 R.sub.11 is H or CH.sub.3 ; PA1 R.sub.12 is C.sub.1 -C.sub.3 alkyl; PA1 R.sub.13 is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.14 is H or CH.sub.3 ; PA1 R.sub.15 is C.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 R.sub.16 is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.17 is C.sub.1 -C.sub.2 alkyl; PA1 R.sub.18 is C.sub.1 -C.sub.3 alkyl or N(CH.sub.3).sub.2 ; PA1 R.sub.19 is C.sub.1 -C.sub.3 alkyl or CH.sub.2 CH.dbd.CH.sub.2 ; PA1 m is 0 or 1; PA1 n is 0 or 2; PA1 Q.sub.1 is O, S or SO.sub.2 ; PA1 Q.sub.2 is O or S; and PA1 W is O, S or SO.sub.2 ; PA1 A is ##STR7## X is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, F, Cl, Br, CF.sub.3 or OCHF.sub.2 ; PA1 T is H, SeCH.sub.3, SeC.sub.6 H.sub.5, SCH.sub.3 or ##STR8## Y is SeCH.sub.3, SeC.sub.6 H.sub.5, ##STR9## OSi(CH.sub.3).sub.3, CH.sub.2 OH or CH.sub.2 OSi(CH.sub.3).sub.3 ; Z is CH or N; PA1 X.sub.1 is CH.sub.3, OCH.sub.3 or OC.sub.2 H.sub.5 ; PA1 E is F, Cl or Br; PA1 G is CH(OCH.sub.3).sub.2, CH(OC.sub.2 H.sub.5).sub.2, ##STR10## or C.sub.6 H.sub.5 ; R.sub.20 is H, CH.sub.3, CF.sub.3, OCH.sub.3, F, Cl, Br or NO.sub.2 ; PA1 p is 0, 1 or 2; and PA1 q is 0, 1 or 2; PA1 (1) when X is F, Cl or Br, then Z is CH; PA1 (2) when m is 1, then R.sub.9 is H; PA1 (3) the sum of p and q is less than or equal to 2; PA1 (4) when A is A-2 and L is L-1, then R.sub.1 is C.sub.2 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkoxy, OCH.sub.2 CH.sub.2 OCH.sub.3, CO.sub.2 R.sub.15, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, OSO.sub.2 R.sub.18, WCF.sub.3, WCHF.sub.2, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or OCH.sub.2 CH.sub.3, C.sub.6 H.sub.5, ##STR11## (5) when A is A-4, then L is L-1, L-2, L-3, L-4, L-5, L-6, L-7, L-8 or L-9; PA1 (6) when A is A-4 and L is L-1, then R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, F, Cl, Br, NO.sub.2, CF.sub.3, CO.sub.2 R.sub.15, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, OSO.sub.2 R.sub.18, S(O).sub.n C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3 or OCH.sub.2 CH.sub.3, C.sub.6 H.sub.5, ##STR12## (7) when A is A-5 and L is L-1, then R.sub.1 is C.sub.2 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkoxy, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3, C.sub.6 H.sub.5, ##STR13## (8) when A is A-5, L is L-1 and R.sub.1 is SO.sub.2 NR.sub.16 R.sub.17 or SO.sub.2 N(OCH.sub.3)CH.sub.3, then E is F or Br; PA1 (9) when A is A-5 and L is L-4, L-5 or L-6, then R.sub.5 is C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, SO.sub.2 NR.sub.16 R.sub.17, SO.sub.2 N(OCH.sub.3)CH.sub.3 or S(O).sub.n R.sub.19 ; PA1 (10) when A is A-5 and L is L-10, L-11, L-12, L-13, L-14, L-15, L-16 or L-17, then E is Cl or Br; PA1 (11) when A is A-5, then L is other than L-8, L-11 or L-17; and PA1 (12) R.sub.13 and R.sub.14 are not simultaneously H; and their agriculturally suitable salts. PA1 (1) Compounds of Formula I where R is H and A is A-1; PA1 (2) Compounds of Preferred 1 where R.sub.2 is H, R.sub.20 is H, X is CH.sub.3 or OCH.sub.3, T is H, p is 0 and q is 0; PA1 (3) Compounds of Preferred 2 where L is L-1, L-5, L-8, L-10, L-11, L-15 or L-17; PA1 (4) Compounds of Preferred 3 where L is L-1 and R.sub.1 is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, Cl, NO.sub.2, CO.sub.2 CH.sub.3, CO.sub.2 C.sub.2 H.sub.5, SO.sub.2 N(CH.sub.3).sub.2, SO.sub.2 CH.sub.3, OSO.sub.2 CH.sub.3 or WCHF.sub.2. PA1 M=alkali metal. PA1 M is an alkali metal; PA1 R' is lower alkyl; and PA1 X.sup.2 is halogen.